This one is for the chronograph lovers. Many enthusiasts argue that every collector needs a chronograph in their collection. It may not be something you keep forever, but it’s a part of the watch world worth experiencing, and the genre likely has more range than any other—more than divers, pilot’s watches, GMTs, and even dress watches. The five watches from five different brands that comprise this list are some of the most timeless examples. Each features a manually wound chronograph caliber, and each has a unique history and the patina to match.
Omega Speedmaster Professional 145.022

It’s no surprise that the Omega Speedmaster Professional takes the top spot on this list. It’s a supremely classic chronograph that has stayed manually wound even as others transitioned to automatic movements. Its dial is inspired by the dashboards of mid-century sports cars, and it’s reliable enough to go to the moon with NASA. It’s also surprisingly wearable with a case that measures 42mm on paper but wears more like a 40mm on the wrist, thanks to a relatively compact lug-to-lug measurement. The reference in the spotlight today is the 145.022, which ran from 1968–1988. The watch features creamy lume on the hands and hour markers as well as subdials full of depth. Ticking inside is the caliber 861, the beating heart of the Speedmaster for decades.
Rolex Daytona 6263

What’s a top 5 list without a Rolex? And what’s a chronograph list without a Daytona? The model has featured an automatic movement since 1988 when it used Zenith El Primero calibers. The brand eventually went in-house starting in the year 2000. The Rolex Daytona is one of the most desirable watches in the world, and a ref. 6263 is perhaps the most widely desirable reference in Daytona history. Smaller than you might expect, the case measures 37mm in diameter with screw-down pushers and a Valjoux 727 beneath the case back. With a range of dial styles and case materials over its nearly two-decade production run, the 6263 offers depth and nearly unmatched collectability that keeps collectors coming back for more.
Breitling Navitimer 806

From an astronaut watch to a racing watch, and now, a tried-and-true pilot’s watch. The Breitling Navitimer is made for the skies and features the busiest dial of the list. Breitling’s slide rule system enables pilots to calculate a bevy of crucial functions mid-air, including speed, distance traveled, and fuel consumption. It’s got more text than a Sunday newspaper, and it’s admittedly not the most user-friendly piece of technology. However, the design is as balanced as it is busy, and the model has cemented itself as an icon in not only watch history but aviation history as well. The Breitling Navitimer 806 is powered by the Venus 176 and measures approximately 41mm in diameter. For an extra dash of historical charm, hunt for a Navitimer with the Aircraft Owners and Pilots Association (AOPA) logo on the dial.
Heuer Bundeswehr Flyback 1550 SG

From a distance, this watch might look more like a diver than a chronograph. That’s even more curious given that it comes from Heuer, a brand known for its racing chronographs. The Heuer Bundeswehr Flyback 1550 SG is neither a diver nor a racing chronograph. The German pilot’s watch, which debuted in 1955, features a wide, rotating bezel and a flyback chronograph movement in the Valjoux 230. Flyback movements are essential for pilots as they cut down on the time needed to stop, reset, and restart the chronograph, thus making any in-flight calculations more accurate and the mission at hand more successful. The 43mm case brings considerable presence to the wrist and only adds to the punchiness of this classic and often underappreciated chronograph.
Zenith Sub Sea Diver A277

Reverse panda dials are becoming a theme on this list as we wrap things up with the Zenith Sub Sea Diver A277. The best-selling Zenith chronograph is without a doubt their legendary El Primero, arguably the world’s first automatic chronograph. And now we know what the brand’s best-selling manually wound chronograph is. The Sub Sea Diver A277 is considered a diver’s chronograph and features a rotating bezel like the aforementioned Heuer. The watch had a rather short production run of only two years and came in two different versions. These factors combine to enhance the collectability of the watch and push it into cult classic territory among enthusiasts.